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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O6
Molecular Weight 300.2635
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSMETIN

SMILES

COc1ccc(cc1O)-c2cc(=O)c3c(cc(cc3o2)O)O

InChI

InChIKey=MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

HIDE SMILES / InChI
Molecular Formula C16H12O6
Molecular Weight 300.2635
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Diosmetin is the aglycone of the flavonoid glycoside diosmin, which occurs naturally in citrus fruits. Diosmetin is found in the legume Acacia farnesiana Wild and Olea europaea L. leaves. Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflammatory activities. Diosmetin increased inhibitory GSK-3beta phosphorylation, while selectively reducing gamma-secretase activity, Abetta generation, tau hyperphosphorylation and pro-inflammatory activation of microglia in vitro, without altering Notch processing. Therefore, diosmetin could be considered as potential candidate for novel anti- Alzheimer's disease therapy. Diosmetin is ER-beta agonist and potential novel drug for the acute myeloid leukemia treatment.

CNS Activity

Originator

Oesterle, O.A.|Wander, G.
1
Sources: DOI: 10.1002/hlca.19250080179

Approval Year

2010
430
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
 140.0 nM [IC50]
Inhibitor
7728
 2.4 µM [IC50]
Inhibitor
7728
 29.0 nM [IC50]
Agonist
2470
Inhibitor
7728
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Preventing
Basic research
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.
2003 May
Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action.
2003 May 1
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
2003 Sep 9
A validated HPLC determination of the flavone aglycone diosmetin in human plasma.
2004 Dec
Metabolism of apigenin by rat liver phase I and phase ii enzymes and by isolated perfused rat liver.
2004 Jan
Antitubercular constituents of Valeriana laxiflora.
2004 Jun
Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships.
2004 Nov 15
[Investigation of the hepatoprotector action of natural flavonoids].
2004 Nov-Dec
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.
2005 Feb 15
Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
2008 Apr 1
Oregano: a source for peroxisome proliferator-activated receptor gamma antagonists.
2008 Dec 24
Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation.
2008 Feb
New features on the fragmentation and differentiation of C-glycosidic flavone isomers by positive electrospray ionization and triple quadrupole mass spectrometry.
2008 Jun
Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway.
2008 Jun
A new ferulic acid ester and other constituents from Dracocephalum peregrinum.
2008 Oct
Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana.
2009 Feb
Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana.
2009 Feb
Simultaneous determination of the flavonoid aglycones diosmetin and hesperetin in human plasma and urine by a validated GC/MS method: in vivo metabolic reduction of diosmetin to hesperetin.
2009 Feb
Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450.
2009 Feb 8
Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation.
2009 Jul
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.
2009 Mar 25
Effects of Various Flavonoids on the α-Synuclein Fibrillation Process.
2010 Jan 28
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.
2010 Jun
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.
2011 May 1
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.
2015 Mar
Patents

Patents

JP2007223914A
1
JP2010521566A
4
JP2011505817A
2
JP4370072B2
48

Sample Use Guides

In Vivo Use Guide
Mice: 50mg /kg/every other day for 6 weeks
Route of Administration: Intraperitoneal
In Vitro Use Guide
Diosmetin caused G1 arrest at 10 microM in MDA-MB 468 cells after 48-h treatment whereas this effect was not observed in MCF-10A cells.
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:24:59 UTC 2021
Edited
by admin
on Sat Jun 26 08:24:59 UTC 2021
Record UNII
TWZ37241OT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIOSMETIN
INCI   MI   WHO-DD  
INCI  
Official Name English
4'-METHYLLUTEOLIN
Common Name English
DIOSMETIN [WHO-DD]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-
Systematic Name English
3',5,7-TRIHYDROXY-4'-METHOXYFLAVONE
Systematic Name English
DIOSMETIN [INCI]
Common Name English
DIOSMETIN [MI]
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)CHROMEN-4-ONE
Systematic Name English
DIOSMETINE
Common Name English
LUTEOLIN-4'-METHYL ETHER
Common Name English
CYANIDENON-4'-METHYL ETHER 1479
Common Name English
DIOSMETOL
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
FLAVONE, 3',5,7-TRIHYDROXY-4'-METHOXY-
Systematic Name English
Classification Tree Code System Code
DSLD 4156 (Number of products:7)
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
Code System Code Type Description
EVMPD
SUB35834
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
HSDB
8101
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
WIKIPEDIA
DIOSMETIN
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
EPA CompTox
520-34-3
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
PUBCHEM
5281612
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
RXCUI
1314347
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY RxNorm
CAS
520-34-3
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
FDA UNII
TWZ37241OT
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
DRUG CENTRAL
4601
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-291-8
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
MERCK INDEX
M4594
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY Merck Index
MESH
C039602
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
DRUG BANK
DB11259
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
Related Record Type Details
AGATHOSMA BETULINA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of DIOSMIN
PARENT -> IMPURITY
NMT 3%
USP
Related Record Type Details
Structure of DIOSMETIN
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